In a continuation of studies of polyketide metabolites, work during the coming year will be concentrated in three areas: 1) Development of biogenetically modelled synthetic methods for preparation of pretetramide and related tetracyclic aromatic metabolites, and the use of these compounds and their synthetic precursors in studies of the biosynthesis of tetracyclines. 2) Studies of the biosynthesis of the naphthoquinone mollisin using a tetrahydroxyphenanthrene which is postulated to be an intermediate in the formation of this fungal metabolite. Biomimetic syntheses will be investigated. 3) New methods for the assembly of polycarbonyl chains will be investigated using four highly reactive new anionic reagents which are being developed in this laboratory.